Diethyl Sulfate → 1-Chloro-3-ethoxy-2-fluorobenzene

HRID 2098998Notes

Reaction equation

HRID 2098998 reaction equation
[Cl:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].S(OCC)(O[CH2:16][CH3:17])(=O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:16][CH3:17])[C:3]=1[F:9]

Participants

4

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 27737123-Chloro-2-fluorophenol

Product 1

HCID 596780871-Chloro-3-ethoxy-2-fluorobenzene

Procedure

The compound (b5) was added dropwise to a reactor having 1,200 g of a 10% sodium hydroxide aqueous solution placed therein over 30 minutes in a temperature range of 20 to 40° C. Thereafter, 462 g of diethyl sulfate was added dropwise thereto over 1 hour in a temperature range of 25 to 35° C., followed by stirring for 5 hours in that temperature range. The resulting organic layer was collected and washed with 200 mL of water in three times, followed by drying, to obtain 505 g of 1-chloro-3-ethoxy-2-fluorobenzene (b44). The resulting liquid was colorless.

Workup

  1. waitover 1 hour in a temperature range of 25 to 35° C.
  2. customThe resulting organic layer was collected
  3. washwashed with 200 mL of water in three times
  4. customby drying

Sources & evidence

ORD record
ord-987832814a6d4de2a92306ae98e01851
Source dataset
uspto-grants-2009_08
Patent number
US07569258B2

Reaction notes

Loading…